Planning family resort vacations: 6 essential questions to ask yourself before you book.

So, you want to go to a resort with the fam on vacation? Lucky you. I just did it and I can help! But first know, that as with most anything that involves tiny humans, tweens, teens — or any combination of them — you’ll need a clear plan. And the best way to start building one is to ask yourself an important question: What kind of vacation do you want to have?

Are you going for easy or adventurous? Do you want it to be laid-back or structured? Basically, what’s going to leave everyone giddy and smiling? (Except for maybe any moody, perma-scowling teenagers who may be in tow. Then again, a great family resort vacation can get them smiling too. )

After spending a great long weekend at a resort with my son that was overall pretty awesome, I’ve put together six big questions I think will be really helpful for you to ask yourself before planning. If you can answer them, I bet it will help you land on the exact perfect family resort vacation for your own brood.

Related: Family travel tips: How to use Airbnb for

your vacation

1. What time of year do you want to go?

Starting with the question of when you want to travel is smart because it can immediately rule out potentially miserable situations. Like visiting a foreign country in the middle of its rainy season, or spending time in an otherwise fantastic vacation city during its inside-the-oven hot season. (Looking at you, Scottsdale.)

Nailing down the “when” also helps you skirt the holiday high season for popular destinations like the Caribbean. Obviously, families are all trying to catch a break during the winter season that lasts from mid-December through about mid-April, so prices everywhere will be highest then. If you’ve got Aruba or Turks and Caicos in mind, consider lining up your family getaway during the Caribbean “shoulder season,” which is late spring and fall.

However, for most families, shoulder season is also school season. Instant scheduling conflict. If you’re not one for pulling your kids out of school for a few days, you could instead aim for low season, which is June through August — or summer in the northern hemisphere. Just know that while you can score big deals and cut costs traveling then, you’ll need to prepare to deal with some potentially sky-high temperatures and humidity numbers.

Like Southern Florida in August is not a game. You’ll basically spend 96 percent of your vacation talking about how damn hot it is and stocking up on Gatorade.

Then again, you may not have the kind of family that’s bothered by extreme temperatures. And consider that while it may officially be sweltering out, when you’re super close to a beach, the shade of some palm trees, and a cold drink with an umbrella in it, that sure does temper the heat.

2. How far do you want to travel?

Say you have three little ones under the age of six. I’d say that taking a 10-hour flight — with two connections — from the east coast to Hawaii for your family resort vacation might not be among the best-laid plans.

We live in New England, and earlier this month I was invited on a fun press trip to Riviera Maya, Mexico, to get a first look at Azul Hotels By Karisma’s new Nick Experience — the result of a major partnership between Nickelodeon and the international beach resort chain that we adore and have written about before. (Liz went to the Azul Beach Hotel outside Cancun with her extended family years ago, and still raves about it.)

I was surprised and rather thrilled to learn that Delta flew direct from Hartford to Cancun airport in four hours, which made the trip so so so much easier than lots of destinations, especially flying solo with my six-year-old son.

The thing is, as we always say, you know your kids best. Maybe your toddlers are pretty great on long flights. Maybe you have tweens who can hang in there with red-eye flights and time-zone jumps. Let your own kids be your guide if you’re considering whether to keep your vacation relatively domestic, with an easy jaunt to a Walt Disney World resort in Orlando, a swanky southwestern resort like The Phoenecian in Scottsdale (which has a great kids club while you hit the spa or the links), or the highly-rated Woodloch Resort in Hawley, Pennsylvania which is just a train or a car ride for me. I haven’t been yet, but from the reviews on Trip Advisor I’d go in a sec.

Or, maybe your situation allows your family to spread your wings a little and head further away. Like visiting Antigua’s St. James’s Club Resort and Villas, or the Four Seasons Resort Costa Rica at Peninsula Papagayo which Kristen still dreams about.

Related: The most helpful family travel tips for parents, from parents who know: Us!

3. Do you want your family resort to be an all-inclusive?

Going the all-inclusive route may seem like a no-brainer, especially when you factor in kids. There are definitely pros to going all-inclusive:

There’s no need to carry money or credit cards in your beach bag

You know before you go how much money the trip will cost (give or take)

No need for buying groceries, cooking, or making lunches (!)

You can often eat as much and as often as you’d like without having to research restaurants

You eliminate the need for a rental car and ground transportation

No need to carry around cash; even if liquor isn’t included you can bill it to your room.

Lots of activities are available right on property

Generally there’s access to a kids’ club and sitting services at family-friendly destinations

Frosty cold alcoholic drinks with umbrellas at the ready

Azul Sensatori Hotel, by Karisma via TripAdvisor

During our stay at Azul Sensatori, it was so nice to have in-room dining available 24 hours a day. What a great amenity if you’re traveling with kids! It especially came in handy our first night there, when my son and I opted for late night quesadillas after dancing the night away (mainly him!) at a Nick Experience welcome party.

However, there are some downsides to consider with an all-inclusive, too:

Dining options and mealtimes may be limited

Quality of food can be meh at many resorts

Reservations may be needed at the on-site restaurants

It can be more expensive, especially if you’re paying full price for young kids or non-drinkers

If you venture off the resort to explore other activities or restaurants, you’re essentially paying for those things twice

Many activities, such as tours, motorized water activities and spa services, are additional.

Be sure to read the fine print on all-inclusive resorts to see if it makes sense for your budget and your level of adventure-seeking. For example, one of the benefits of an all-inclusive Club Med vacation is phenomenal food, plenty of seating, and no need for reservations; other all-inclusives will differ.

Figuring out what works best for your family is always easiest when you have all the info in front of you.

4. What are the food options at the family resort?

As I started to touch on above, if you go for the all-inclusive experience, make sure you know what to expect from the dining options there, since we all know this can be a huge deal when you’ve got picky kids in tow. Is the resort all buffets or à la carte restaurants? Will the food be authentic to the locale you’re visiting or are we talking all-fried everything with ketchup on the side?

Often resorts will try to cater to “American tastes” with faux international cuisine or straight-up fast food chain-style offerings, as was the case with my editor Liz’s trip to Atlantis Bahamas, where Johnny Rockets was basically the go-to lunch spot.

Let’s just say that was not a selling point for her; she is a bigger fan of Club Med, where the chefs are European trained and the buffet food is as good as any sit-down dinner at other resorts.

Thankfully, the whole lackluster food thing wasn’t an issue on my Riviera Maya trip. Azul Sensatori Hotel is a Gourmet Inclusive Resort — a Karisma trademark perk, evidently — which means the level of attention paid to the food’s prep and taste is high at its six, no-reservations-needed restaurants.

Our hotel even had nice touches for the kids, like chocolate milk smoothies and the happy pancake, above, which was served during the character breakfast. That’s where Nickelodeon stars like Dora the Explorer and SpongeBob SquarePants showed up for a little song and dance (literally). In case you’re wondering whether Disney has a lock on the character breakfast. More on that stuff later.

Related: 13 smart tips for a great Disney World vacation with a baby

5. Does the resort have family-centric amenities?

Imagine rolling up to your summer vacation at a sunny resort with just a couple of pieces of luggage and your child in hand? I’m talking no stroller, no travel crib, no baby food jars or pouches, no bottle warmer, and no — wait for it — diapers.

Whuuuut? Girl, yes. It’s possible.

At the Azul Beach Hotel (a smaller, slightly elevated luxury sister to the nearby Azul Sensatori), guests traveling with young kids can leave all the gear at home. The hotel transport staff will happily meets you at the airport with a stroller, and the family suites are outfitted with everything parents of young’uns would need from change tables and baby monitors to bottle sterilizers and stepping stools for the bathroom sink. Azul Hotels also feature freshly pureed baby food served on pint-sized china. Awww, right?

The teeny bathrobes and slippers in the rooms and the kid-sized lounge chairs around the pools are super cute. I also like that this Azul resort has a special kids’ check-in complete with a green “slime” smoothies, plus Nickelodeon Concierges and a Nick Toy Lending Library. It all goes toward helping kids feel welcome and part of the relaxing fun.

Of course not every resort will be quite so comprehensive, but you should still double check to see what’s what before you go. Think portable cribs, baby food, strollers, bottle sterilizers, and other essential gear.

Also be sure to ask whether it will cost you extra. It’s kind of nice not to have to pack an extra suitcase for diapers; but on the other hand, if diapers cost three times more a pack than they do it home, you might find it’s still cheaper than the baggage check fee to bring your own.

Related: Tips for traveling with baby on the first vacation

6. Does the family resort have child care or kids clubs? And are they the kind that are right for you?

This may be the most contested question about family travel — how much time do you spend with the kids versus time spent as a family?

That answer is totally up to you. But I’d imagine that once your kids are old enough to have an opinion about such things — like, three — they may want to spend a little more time with kids their own age than with their parents. (Sniff. It does happen.)

Most family resorts wisely have a complimentary kids’ club with some pretty amazing activities. I tracked down a a pirate dress-up and treasure hunt at the Blockade Runner Beach Resort in Wrightsville Beach, North Carolina; coconut art crafts and making homemade volcanoes at the Fairmont Kea Lani in Maui; and horseback riding, stargazing and pizza-movie nights at the Sandestin Golf and Beach Resort in Miramar Beach, Florida. Pretty cool.

As for the Azul Sensatori, their newly renovated kids’ club, Azulitos Playhouse, happens to be rather impressive. It’s for kids ages 4-12 and is sectioned off into basically everything a kid would be down to do: LEGOs, dollhouse, running and tumbling, movies, video games. You can even get slimed, Nick-style. Plus, the playhouse hosts daily Nickelodeon-themed activities supervised by childcare staff to keep your youngster busy from morning until late afternoon, when the playhouse stays open for family time, which means no staff supervision.

There’s also a separate teens club for kids 13-17 years old with a state-of-the-art gaming room (comparable to the impressive one at Atlantis), air hockey, the latest game consoles, daily activities, and a Teens Corner, which is a non-alcoholic bar and disco.

This is a huge thing, as you parents of tweens and teens know. The same cute arts and crafts that entertain the little ones just don’t have the same appeal for older kids. But then, you may want to decide just how much video gaming and indoor activity you want for your kids. One thing Liz liked about visiting Club Med Punta Cana a few years ago, is that the arcade actually closes during the day to make sure kids are outside enjoying the pool, the beach, and water sports instead.

When you are looking into a club for little ones though, parents should decide how deep into cartoons and characters they want to go before planning the family’s resort vacation. There are plenty of resorts with kids clubs that aren’t based on favorite TV or movie characters; then on the other end is a Disney Cruise, where pretty much every on-board experience will have some sort of branding, right down to the wall art and the iconic mouse-shaped pancakes.

I like the idea of something in the middle, and I found the Nick Experience to be fun, with just enough kid-character stuff; not overbearing at all. Then, there were enough cartoon-free zones where I could relax like an adult. Still, Nick does skew a little young by definition. I could see a 10-year-old being thoroughly unimpressed with the Teenage Mutant Ninja Turtles showing up on stage at the evening’s dance party. Although I must say, those four talking turtles did do The Wobble when we saw them.

Come on. That’s pretty impressive.

Our thanks to Karisma for including Cool Mom Picks on their press trip and covering transportation, hotel, and some expenses. For more information about how to book a family resort vacation at Azul Sensatori Hotel or any Karisma resort, check their website. Also, we suggest following Azul on Facebook or Twitter, where you’ll frequently find fantastic deals, especially for families.

If you have questions about any of the hotels and resorts we’ve mentioned here, feel free to leave them in the comments and we’ll be happy to answer them.